Cesium carbonate → 1-(4-Chloro-5,7-difluoro-3-methylquinolin-2-yl)-5,5-dimethylpiperidin-2-one

Participants

Role	Name	HCID	Charge
Reactant	Cesium carbonate	HCID 10796	—
Reactant	1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)	HCID 636044	—
Reactant	5,5-Dimethylpiperidin-2-one	HCID 10479660	—
Reactant	2,4-Dichloro-5,7-difluoro-3-methylquinoline	HCID 59631040	—
Catalyst	Bis(dibenzylideneacetone)palladium	HCID 9811564	—
Solvent	Dichloromethane	HCID 6344	—
Solvent	Ethyl Acetate	HCID 8857	—
Solvent	1,4-Dioxane	HCID 31275	—
Product	1-(4-Chloro-5,7-difluoro-3-methylquinolin-2-yl)-5,5-dimethylpiperidin-2-one	HCID 59631203	—

Reaction Conditions

Temperature	100 °C

Reaction Steps

XantPhos (273 mg, 0.472 mmol), 2,4-dichloro-5,7-difluoro-3-methylquinoline (780 mg, 3.20 mmol), 5,5-dimethylpiperidin-2-one (400 mg, 3.20 mmol), cesium carbonate (1.40 g, 4.40 mmol) and Pd2(dba)3 (140 mg, 0.160 mmol) was slurried in 1,4-dioxane (8.5 mL) and heated in a microwave reactor at 100° C. for 3 h. The reaction was cooled to rt and then diluted with EtOAc and DCM. The slurry was then filtered and concentrated. The residue was purified by column chromatography (silica gel, 0 to 50% EtOAc:DCM) to give 1-(4-chloro-5,7-difluoro-3-methylquinolin-2-yl)-5,5-dimethylpiperidin-2-one. Mass Spectrum (ESI) m/e=339.1 (M+1).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08765940B2
Source dataset	uspto-grants-2014_07
ORD ID	ord-3af9e594ae674cc684d1e47bef10ed7a
Source note	uspto-grants-2014_07